Sodium Carbonate → 2-(2-Formyl-biphenyl-4-yloxy)4-trifluoromethyl-benzonitrile

HRID 1243690Notes

Reaction equation

HRID 1243690 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[CH:21]=[O:22].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:21]([C:3]1[CH:4]=[C:5]([O:6][C:7]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[CH:19]=[CH:20][C:2]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 219303662-(4-Bromo-3-formyl-phenoxy)-4-trifluoromethyl-benzonitrile

Product 1

HCID 219303872-(2-Formyl-biphenyl-4-yloxy)4-trifluoromethyl-benzonitrileYield 99%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 2-(4-bromo-3-formyl-phenoxy)-4-trifluoromethyl-benzonitrile (1.76 g, 4.76 mmol) and Pd(dba)3 (21.8 mg, 5 mole %) in dimethoxyethane (15 ml) was added a solution of phenylboronic acid (609 mg, 5 mmol), triphenylphosphine (15 mg, 12 mole %) and sodium carbonate (530 mg, 5 mmol) in water (10 ml). The mixture was refluxed for 3 h. The solvent was evaporated off and the aqueous layer was extracted with dichloromethane. The extracts were dried with MgSO4 and filtered through silica. Evaporation yielded a brown solid (1.73 g, 99%).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe solvent was evaporated off
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialThe extracts were dried with MgSO4
  5. filtrationfiltered through silica
  6. customEvaporation

Sources & evidence

ORD record
ord-13b4b155fc574d2ba9bbacb2c540c92b
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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